Like so many geeks these days, I’m living my life inside of plain text files. Rather than rehash all the benefits, I’ll just link to Michael Schechter, but the biggest benefit is portability. I’ve found a system that works, for the most part, to keep my life in sync, based around Dropbox, nvALT, and any of a growing number of Dropbox-enabled iOS text editors. [1] As long as I don’t try to futz with it, it works fine.

Like any geek, however, I find excuses to futz.

It all started when I decided I wanted to give Simplenote a second chance, after seeing Patrick Rhone endorse it on App.Net. I quickly realized it didn’t work the way I wanted, so I decided to ditch it. It’s perfectly possible to live in Simplenote if you don’t want to use anything else. The moment I tried introducing other applications into this, all hell broke loose. The first problem came when, while trying to extricate Simplenote from my workflow, it populated my note folder with duplicates upon duplicates of files, because of a quirk in the way nvALT stores its synchronization settings. I ended up having to pull the recent documents out of the folder, and restore my text files from a Time Machine backup. Thinking this was the end of it, I happily went about my life for a few weeks, until I wanted to do some editing on my iPad in WriteRoom.

Apparently, the way WriteRoom synchronizes documents involves keeping a copy of everything on my device. Launching WriteRoom to do some work on a document I’d created in Drafts resulted in it trying to synchronize over 1,000 plain text files into my Dropbox folder that it had picked up during my tryst with Simplenote—though I failed to realize it at the time. I just figured that, since I hadn’t launched WriteRoom in a while, it was taking its time synchronizing all the stuff in my Dropbox folder. Eventually, fed up with the time it was taking, I reinstalled Byword, and did my editing in there. The magnitude of the problem didn’t hit until I got to work and found an error message form nvALT about being unable to load my files. Near as I can tell, Writeroom not only dumped 1,000 some odd text files—mostly duplicates—into my Dropbox, but it also overwrote nvALT’s settings file.

All this shows the shortcomings still inherent in keeping data, any form of data, in sync across multiple devices and applications. I don’t envy developers who have to muck about with either iCloud, or writing their own solution. [2] The myriad of things that can go wrong, handling every potential exception, even the best team of developers will have issues. Frustrating as it is to be Bare Bones Software, and unable to hook Yojimbo up to iCloud and have it work, it’s a minor miracle that even the stuff that does work, like Dropbox or Simplenote, actually works. Just make you back everything up, regularly.